Chemoenzymatic synthesis of fluorinated carbohydrates: 2-deoxy-2-fluoro-D-glucose and 5-deoxy-5-fluoro-manno-γ-lactol

Article abstract of DOI:10.1016/S0040-4020(97)00746-1

Two fluorinated hexoses were prepared from optically active cis-diols 1, which were obtained by microbial oxidation of the corresponding halobenzenes with E. coli JM109 (pDTG 601). The stereochemistry of the products was controlled by careful introduction of fluorine onto the periphery of the cis-diols via opening of epoxides with tetrabutylphosphoniumfluoride dihydrofluoride (TBPF-DF). Oxidative cleavage of the cyclohexene skeleton followed by reductive cyclization led to the fluorinated hexoses.